Copolymerized methine colorant-polyester color concentrates

Abstract

Disclose are polyester color concentrates, especially amorphous and partially-crystalline, polyester color concentrates, comprising a polyester having copolymerized therein colored residues of at least one polyester-reactive, thermally-stable methine colorant compound. The color concentrates may be used to impart yellow shades and colors to various polymeric materials, shaped articles fabricated of and coatings formulated from such polymeric materials and, especially, personal, medical and home care products where non-extractability of the colorant material is essential. Also disclosed are colored semicrystalline powders derived from the color concentrates.

We claim: 
     
       1. A color concentrate comprising a polyester having copolymerized therein at least 1.0 weight percent, based on the weight of the concentrate, of the residue of one or more methine colorant compounds having the formula ##STR83## wherein A is an aniline, 1,2,3,4-tetrahydroquinoline, 2,3-dihydro-1,4-benzoxazine or 2,3-dihydroindole residue of a methine colorant compound bearing one polyester. reactive substituent; and B is an unsubstituted or substituted alkoxycarbonyl radical or an aromatic, carbocyclic or heterocyclic radical bearing one polyester-reactive substituent.   
     
     
       2. A color concentrate according to claim 1 comprising a polyester having an inherent viscosity of at least 0.20 having copolymerized therein at least 5.0 weight percent, based on the weight of the concentrate, of the residue of one or more methine colorant compounds having the formula: ##STR84## wherein B is a radical having the formula: ##STR85## wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below; R 1  is lower alkyl, lower alkoxy or halogen;   R 2  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical devoid of polyester-reactive groups;   R 3  is a divalent organic group;   n is 0, 1, 2 or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR86## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical.   
     
     
       3. A color concentrate according to claim 1 comprising a polyester having an inherent viscosity of at least 0.20 having copolymerized therein about 10 to 40 weight percent, based on the weight of the polyester, of the residue of one or more methine colorant compounds having the formula: ##STR87## wherein R 1  is hydrogen , methoxy, ethoxy, or chloro; R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 3  --X is alkylene-OH, alkylene-O-alkylene-OH, ##STR88##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   R 18  is lower alkyl.   
     
     
       4. A color concentrate according to claim 1 comprising a polyester having an inherent viscosity of at least 0.20 having copolymerized therein at least 5.0 weight percent, based on the weight of the concentrate, of the residue of one or more methine colorant compounds having the formula: ##STR89## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro; R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 18  is lower alkyl.   
     
     
       5. A color concentrate according to claim 1 comprising a polyester having an inherent viscosity of at least 0.20 having copolymerized therein at least 5.0 weight percent, based on the weight of the concentrate, of the residue of one or more methine colorant compounds having the formula: ##STR90## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro; R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 18  is lower alkyl.   R 19  is alkylene, alkylene-O-alkylene, alkylene-SO 2  -alkylene, alkylene-phenylene-alkylene, alkylene-O-phenylene-alkylene, ##STR91##   
     
     
       6. A color concentrate according to claim 1 comprising a polyester having an inherent viscosity of at least 0.20 having copolymerized therein at least 5.0 weight percent, based on the weight of the concentrate, of the residue of one or more methine colorant compounds having the formula: ##STR92## wherein B is a radical having the formula: ##STR93##  wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below; R 1  is lower alkyl, lower alkoxy or halogen;   R 3  is a divalent organic group;   R 4 , R 5 , and R 6  are the same or different and each represents hydrogen or lower alkyl;   n is 0, 1, 2 or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR94## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical.   
     
     
       7. A color concentrate according to claim 1 comprising a polyester having an inherent viscosity of at least 0.20 having copolymerized therein about 10 to 40 weight percent, based on the weight of the polyester, of the residue of one or more methine colorant compounds having the formula: ##STR95## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro; R 3  -X is alkylene-OH, alkylene-O-alkylene-OH, ##STR96##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   R 5  and R 6  each is hydrogen or methyl; and   R 18  is lower alkyl   
     
     
       8. A color concentrate according to claim I comprising a polyester having an inherent viscosity of at least 0.20 having copolymerized therein at least 5.0 weight percent, based on the weight of the concentrate, of the residue of one or more methine colorant compounds having the formula: ##STR97## wherein B is a radical having the formula: ##STR98##  wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below; R 1  is lower alkyl, lower alkoxy or halogen;   R 3  is a divalent organic group;   R 4  and R 5  are the same or different and each represents hydrogen or lower alkyl;   n is 0, 1, 2, or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR99## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical.   
     
     
       9. A color concentrate according to claim 8 wherein the polyester has copolymerized therein about 10 to 40 weight percent of the residue of one or more of the methine colorant and wherein: B is a radical having the formula ##STR100##  wherein R 18  is lower alkyl; R 1  is methyl, methoxy, ethoxy, or chloro; and   n is 0 or 1;   R 3  -X is alkylene-OH, alkylene-O-alkylene-OH, ##STR101##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   
     
     
       10. A color concentrate according to claim 1 comprising a polyester having an inherent viscosity of at least 0.20 having copolymerized therein at least 5.0 weight percent, based on the weight of the concentrate, of the residue of one or more methine colorant compounds having the formula: ##STR102## wherein B is a radical having the formula: ##STR103##  wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below; R 1  is lower alkyl, lower alkoxy or halogen;   R 3  is a divalent organic group;   R 6  is hydrogen or lower alkyl;   R 4  and R 5  are the same or different and each represents lower alkyl or an unsubstituted or substituted aryl radical; and   n is 0, 1, 2, or 3;   X is hydroxy, carboxy or an ester radical having the formula: ##STR104## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical.   
     
     
       11. A color concentrate according to claim 10 wherein the polyester has copolymerized therein about 10 to 40 weight percent of the residue of one or more of the methine colorant and wherein: B is a radical having the formula ##STR105##  wherein R 18  is lower alkyl; R 1  is methyl, methoxy, ethoxy, or chloro; and   n is 0 or 1;   R 3  -X is alkylene-OH, alkylene-O-alkylene-OH, ##STR106##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   
     
     
       12. A color concentrate according to claim 1 comprising a polyester having an inherent viscosity of at least 0.20 having copolymerized therein at least 5.0 weight percent, based on the weight of the concentrate, of the residue of one or more methine colorant compounds having the formula: ##STR107## wherein B is a radical having the formula: ##STR108##  wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below; R 1  is lower alkyl, lower alkoxy or halogen;   R 3  is a divalent organic group;   R 7  and R 8  are the same or different and each represents lower alkyl or an unsubstituted or substituted aryl radical; and   n is 0, 1, 2, or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR109## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical.   
     
     
       13. An amorphous color concentrate comprising an amorphous polyester having copolymerized therein at least 5.0 weight percent, based on the weight of the concentrate, of the residue of one or more methine colorant compounds having the formula: ##STR110## wherein A is an aniline, 1,2,3,4-tetrahydroquinoline, 2,3-dihydro-1,4-benzoxazine or 2,3-dihydroindole residue of a methine colorant compound bearing one polyester-reactive substituent; and B is an unsubstituted or substituted alkoxycarbonyl radical or an aromatic, carbocyclic or heterocyclic radical bearing one polyester-reactive substituent.   
     
     
       14. An amorphous color concentrate according to claim 13 comprising a polyester having an inherent viscosity of at least 0.20 comprised of: (i) diacid residues comprised of at least 50 mole percent terephthalic and/or 2,6-naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 50 mole percent of the residue of a diol having the formula: ##STR111##  wherein R 20  is hydrogen or lower alkyl and R 21  is lower alkyl; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR112## wherein B is a radical having the formula: ##STR113## wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below;   R 1  is lower alkyl, lower alkoxy or halogen;   R 2  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical devoid of polyester-reactive groups;   R 3  is a divalent organic group;   n is 0, 1, 2 or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR114## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical; provided that component (iii) constitutes at least 5.0 weight percent of the concentrate.   
     
     
       15. An amorphous color concentrate according to claim 13 comprising a polyester having an inherent viscosity of 0.20 to 0.80 and a melting temperature of at least 110° C. comprised of: (i) diacid residues comprised of at least 80 mole percent terephthalic and/or 2,6-naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 80 mole percent of the residue of a diol having the formula: ##STR115## (iii) residues of one or more methine colorant compounds having the formula: ##STR116## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 3  -X is alkylene-OH, alkylene-O-alkylene-OH, ##STR117##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   R 18  is lower alkyl; provided that component (iii) constitutes about 10 to 40 weight percent of the concentrate.   
     
     
       16. An amorphous color concentrate according to claim 13 comprising a polyester having an inherent viscosity of 0.20 to 0.80 and a melting temperature of at least 110° C. comprised of: (i) diacid residues comprised of at least 80 mole percent terephthalic and/or 2,6-naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 80 mole percent of the residue of a diol having the formula: ##STR118## (iii) residues of one or more methine colorant compounds having the formula: ##STR119## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 18  is lower alkyl; provided that component (iii) constitutes about 10 to 40 weight percent of the concentrate.   
     
     
       17. An amorphous color concentrate according to claim 13 comprising a polyester having an inherent viscosity of 0.20 to 0.80 and a melting temperature of at least 110° C. comprised of: (i) diacid residues comprised of at least 80 mole percent terephthalic and/or 2,6-naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 80 mole percent of the residue of a diol having the formula: ##STR120## (iii) residues of one or more methine colorant compounds having the formula: ##STR121## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 18  is lower alkyl;   R 19  is alkylene, alkylene-O-alkylene, alkylene-SO 2  -alkylene, alkylene-phenylene-alkylene, alkylene-O-phenylene-alkylene, ##STR122##  provided that component (iii) constitutes about 10 to 40 weight percent of the concentrate.   
     
     
       18. An amorphous color concentrate according to claim 13 comprising a polyester having an inherent viscosity of at least 0.20 comprised of: (i) diacid residues comprised of at least 50 mole percent terephthalic and/or 2,6-naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 50 mole percent of the residue of a diol having the formula: ##STR123## wherein R 20  is hydrogen or lower alkyl and R 21  is lower alkyl; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR124## wherein B is a radical having the formula: ##STR125##  wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below;   R 1  is lower alkyl, lower alkoxy or halogen;   R 3  is a divalent organic group;   R 4 , R 5 , and R 6  are the same or different and each represents hydrogen or lower alkyl;   n is 0, 1, 2 or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR126## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical; provided that component (iii) constitutes at least 5.0 weight percent of the concentrate.   
     
     
       19. An amorphous color concentrate according to claim 13 comprising a polyester having an inherent viscosity of 0.20 to 0.80 and a melting temperature of at least 110° C. comprised of: (i) diacid residues comprised of at least 80 mole percent terephthalic and/or 2,6-naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 80 mole percent of the residue of a diol having the formula: ##STR127## (iii) residues of one or more methine colorant compounds having the formula: ##STR128## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 3  -X is alkylene-OH, alkylene-O-alkylene-OH, ##STR129##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   R 5  and R 6  each is hydrogen or methyl; and   R 18  is lower alkyl; provided that component (iii) constitutes about 10 to 40 weight percent of the concentrate.   
     
     
       20. A partially-crystalline polyester color concentrate comprised of: (i) diacid residues consisting of at least 80 mole percent terephthalic acid residues,   2,6-naphthalenedicarboxylic acid residues,   1,3-cyclohexanedicarboxylic acid residues,   1,4-cyclohexanedicarboxylic acid residues or a mixture thereof; (ii) diol residues consisting of at least 50 mole percent of residues having the formula: --O--(CH 2 ) p  --O--wherein p is 2 to 12; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR130##  wherein A is an aniline, 1,2,3,4-tetrahydroquinoline, 2,3-dihydro-1,4-benzoxazine or 2,3-dihydroindole residue of a methine colorant compound bearing one polyester-reactive substituent; and   B is an unsubstituted or substituted alkoxycarbonyl radical or an aromatic, carbocyclic or heterocyclic radical bearing one polyester-reactive substituent; provided that component (iii) constitutes at least 5.0 weight percent of the concentrate.     
     
     
       21. A partially-crystalline polyester color concentrate according to claim 20 comprised of: (i) diacid residues consisting of at least 80 mole percent terephthalic acid residues;   (ii) diol residues consisting of at least 80 mole percent of residues of having the formula --O--(CH 2 ) p  --O--wherein p is 4 to 12; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR131##  wherein B is a radical having the formula: ##STR132##  wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below;   R 1  is lower alkyl, lower alkoxy or halogen;   R 2  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical devoid of polyester-reactive groups;   R 3  is a divalent organic group;   n is 0, 1, 2 or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR133## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical; provided that component (iii) constitutes at least 5.0 weight percent of concentrate.   
     
     
       22. A partially-crystalline polyester color concentrate according to claim 21 wherein residues (iii) are derived from one or more methine colorant compounds having the formula: ##STR134## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro; R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 3  -X is alkylene-OH, alkylene-0.alkylene-OH, ##STR135##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   R 18  is lower alkyl;   and wherein component (iii) constitutes about 10 to 40 weight percent of the concentrate.   
     
     
       23. A partially-crystalline polyester color concentrate according to claim 21 wherein residues (ii) have the formula --O--(CH 2 ) 4  --O--and residues (iii) are derived from one or more methine colorant compounds having the formula: ##STR136## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro; R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 18  is lower alkyl; and wherein component (iii) constitutes about 10 to 40 weight percent of the concentrate.   
     
     
       24. A partially-crystalline polyester color concentrate according to claim 21 wherein residues (iii) are derived from one or more methine colorant compounds having the formula: ##STR137## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro; R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 18  is lower alkyl;   R 19  is alkylene, alkylene-O-alkylene, alkylene-SO 2  -alkylene, alkylene-phenylene-alkylene, alkylene-O-phenylene-alkylene, ##STR138##  and wherein component (iii) constitutes about 10 to 40 weight percent of the concentrate.   
     
     
       25. A partially-crystalline polyester color concentrate according to claim 20 comprised of: (i) diacid residues consisting of at least 80 mole percent terephthalic acid residues;   (ii) diol residues consisting of at least 80 mole percent of residues having the formula -O-(CH 2 ) p  -O-wherein p is 4 to 12; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR139## wherein B is a radical having the formula: ##STR140##  wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below;   R 1  is lower alkyl, lower alkoxy or halogen;   R 3  is a divalent organic group;   R 4 , R 5 , and R 6  are the same or different and each represents hydrogen or lower alkyl;   n is 0, 1, 2 or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR141## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical; provided that component (iii) constitutes at least 1.0 weight percent of concentrate.   
     
     
       26. A partially-crystalline polyester color concentrate according to claim 25 wherein residues (ii) have the formula -O-(CH 2 ) 4  -O- and residues (iii) are derived from one or more methine colorant compounds having the formula: ##STR142## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro; R 3  -X is alkylene-OH, alkylene-O-alkylene-OH, ##STR143##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   R 5  and R 6  each is hydrogen or methyl; and   R 18  is lower alkyl;   and wherein component (iii) constitutes about 10 to 40 weight percent of the concentrate.   
     
     
       27. A colored semicrystalline powder having an average particle size of less than 30 microns comprising a normally-amorphous polyester which has been modified by dissolution-crystallization-precipitation to impart crystallinity thereto having copolymerized therein at least 5.0 weight percent, based on the weight of the concentrate, of the residue of one or more methine colorant compounds having the formula: ##STR144## wherein A is an aniline, 1,2,3,4-tetrahydroquinoline, 2,3-dihydro-1,4-benzoxazine or 2,3-dihydroindole residue of a methine colorant compound bearing one polyester-reactive substituent; and B is an unsubstituted or substituted alkoxycarbonyl radical or an aromatic, carbocyclic or heterocyclic radical bearing one polyester-reactive substituent.   
     
     
       28. A colored semicrystalline powder according to claim 27 comprising a polyester having an inherent viscosity of at least 0.20 comprised of: (i) diacid residues comprised of at least 50 mole percent terephthalic and/or 2,6-naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 50 mole percent of the residue of a diol having the formula: ##STR145##  wherein R 20  is hydrogen or lower alkyl and R 21  is lower alkyl; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR146## wherein B is a radical having the formula: ##STR147##  wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below;   R 1  is lower alkyl, lower alkoxy or halogen;   R 2  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical devoid of polyester-reactive groups;   R 3  is a divalent organic group;   n is 0, 1, 2 or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR148## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical; provided that component (iii) constitutes at least 5.0 weight percent of the concentrate.   
     
     
       29. A colored semicrystalline powder according to claim 27 having an average particle size of less than 30 microns comprising a normally-amorphous polyester which has been modified by dissolution-crystallization. precipitation to impart crystallinity thereto comprised of: (i) diacid residues comprised of at least 80 mole percent terephthalic and/or 2,6-naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 80 mole percent of the residue of a diol having the formula: ##STR149## (iii) residues of one or more methine colorant compounds having the formula: ##STR150##  wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 3  -X is alkylene-OH, alkylene-O-alkylene-OH, ##STR151##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   R 18  is lower alkyl; provided that component (iii) constitutes about 10 to 40 weight percent of concentrate.   
     
     
       30. A colored semicrystalline powder according to claim 27 having an average particle size of less than 30 microns comprising a normally-amorphous polyester which has been modified by dissolution-crystallization-precipitation to impart crystallinity thereto comprised of: (i) diacid residues comprised of at least 80 mole percent terephthalic and/or 2,6-naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 80 mole percent of the residue of a diol having the formula: ##STR152##  wherein R 20  is hydrogen or lower alkyl and R 21  is lower alkyl; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR153## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 18  is lower alkyl; provided that component (iii) constitutes about 10 to 40 weight percent of concentrate.   
     
     
       31. A colored semicrystalline powder according to claim 27 having an average particle size of less than 30 microns comprising a normally-amorphous polyester which has been modified by dissolution-crystallization-precipitation to impart crystallinity thereto comprised of: (i) diacid residues comprised of at least 80 mole percent terephthalic and/or 2,6-naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 80 mole percent of the residue of a diol having the formula: ##STR154## wherein R 20  is hydrogen or lower alkyl and R 21  is lower alkyl; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR155## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 18  is lower alkyl;   R 19  is alkylene, alkylene-O-alkylene, alkylene-SO 2  -alkylene, alkylene-phenylene-alkylene, alkylene-O-phenylene-alkylene, ##STR156##  provided that component (iii) constitutes about 10 to 40 weight percent of concentrate.   
     
     
       32. A colored semicrystalline powder according to claim 27 comprising a polyester having an inherent viscosity of at least 0.20 comprised of: (i) diacid residues comprised of at least 50 mole percent terephthalic and/or 2,6.naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 50 mole percent of the residue of a diol having the formula: ##STR157## (iii) residues of one or more methine colorant compounds having the formula: ##STR158## wherein B is a radical having the formula: ##STR159##  wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below;   R 1  is lower alkyl, lower alkoxy or halogen;   R 3  is a divalent organic group;   R 4 , R 5 , and R 6  are the same or different and each represents hydrogen or lower alkyl;   n is 0, 1, 2 or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR160## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical; provided that component (iii) constitutes at least 5.0 weight percent of the concentrate.   
     
     
       33. A colored semicrystalline powder according to claim 27 having an average particle size of less than 30 microns comprising a normally-amorphous polyester which has been modified by dissolution-crystallization precipitation to impart crystallinity thereto comprised of: (i) diacid residues comprised of at least 80 mole percent terephthalic and/or 2,6-naphthalene-dicarboxylic acid residues;   (ii) diol residues comprised of at least 80 mole percent of the residue of a diol having the formula: ##STR161## (iii) residues of one or more methine colorant compounds having the formula: ##STR162##  wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 3  -X is alkylene-OH, alkylene-O-alkylene-OH, ##STR163##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   R 5  and R 6  each is hydrogen or methyl; and   R 18  is lower alkyl; provided that component (iii) constitutes about 10 to 40 weight percent of concentrate.   
     
     
       34. A colored semicrystalline powder having an average particle size of less than 30 microns comprising a partially-crystalline polyester which had been modified by dissolution-crystallization-precipitation to impart increased crystallinity thereto comprised of: (i) diacid residues consisting of at least 80 mole percent terephthalic acid residues, 2,6-naphthalene-dicarboxylic acid residues, 1,3-cyclohexanedicarboxylic acid residues, 1,4-cyclohexanedicarboxylic acid residues or a mixture thereof;   (ii) diol residues consisting of at least 50 mole percent of residues having the formula -O-(CH 2 ) p  -O-wherein p is 2 to 12; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR164## wherein A is an aniline, 1,2,3,4-tetrahydroquinoline, 2,3-dihydro-1,4-benzoxazine or 2,3-dihydroindole residue of a methine colorant compound bearing one polyester-reactive substituent; and   B is an unsubstituted or substituted alkoxycarbonyl radical or an aromatic, carbocyclic or heterocyclic radical bearing one polyester-reactive substituent; provided that component (iii) constitutes at least 5.0 weight percent of the concentrate.   
     
     
       35. A colored semicrystalline powder having an average particle size of less than 30 microns comprising a partially-crystalline polyester which had been modified by dissolution-crystallization-precipitation to impart increased crystallinity thereto comprised of: (i) diacid residues consisting of at least 80 mole percent terephthalic acid residues, 2,6-naphthalene-dicarboxylic acid residues, 1,3-cyclohexanedicarboxylic acid residues, 1,4-cyclohexanedicarboxylic acid residues or a mixture thereof;   (ii) diol residues consisting of at least 50 mole percent of residues having the formula -O-(CH 2 ) p  -O-wherein p is 4 to 12; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR165##  wherein B is a radical having the formula: ##STR166##  wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below;   R 1  is lower alkyl, lower alkoxy or halogen;   R 2  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical devoid of polyester-reactive groups;   R 3  is a divalent organic group;   n is 0, 1, 2 or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR167##  wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical; provided that component (iii) constitutes at least 51.0 weight percent of the concentrate.   
     
     
       36. A colored semicrystalline powder according to claim 34 comprising a polyester having an inherent viscosity of at least 0.20 and a melting temperature of at least 110° C. comprised of: (i) diacid residues consisting of at least 80 mole percent terephthalic acid residues;   (ii) diol residues consisting of at least 80 mole percent of residues of 1,4-butanediol; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR168##  wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 3  -X is alkylene-OH, alkylene-O-alkylene-OH, ##STR169##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   R 18  is lower alkyl; provided that component (iii) constitutes about 10 to 40 weight percent of concentrate.   
     
     
       37. A colored semicrystalline powder according to claim 34 comprising a polyester having an inherent viscosity of at least 0.20 and a melting temperature of at least 110° C. comprised of: (i) diacid residues consisting of at least 80 mole percent terephthalic acid residues;   (ii) diol residues consisting of at least 80 mole percent of residues having the formula -O-(CH 2 ) p  -O-wherein p is 4 to 12; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR170##  wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 18  is lower alkyl; provided that component (iii) constitutes about 10 to 40 weight percent of concentrate.   
     
     
       38. A colored semicrystalline powder according to claim 34 comprising a polyester having an inherent viscosity of at least 0.20 and a melting temperature of at least 110° C. comprised of: (i) diacid residues consisting of at least 80 mole percent terephthalic acid residues;   (ii) diol residues consisting of at least 80 mole percent of residues having the formula -O-(CH2) p  -O-wherein p is 4 to 12; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR171## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 2  is lower alkyl; lower alkyl substituted with cyclohexyl, phenyl, phenoxy, lower alkoxy, halogen or cyano; allyl; cyclohexyl; or phenyl;   R 18  is lower alkyl;   R 19  is alkylene, alkylene-O-alkylene, alkylene-SO 2  -alkylene, alkylene-phenylene-alkylene, alkylene-O-phenylene-alkylene, ##STR172##  provided that component (iii) constitutes about 10 to 40 weight percent of concentrate.   
     
     
       39. A colored semicrystalline powder having an average particle size of less than 30 microns comprising a partially-crystalline polyester which had been modified by dissolution-crystallization-precipitation to impart increased crystallinity thereto comprised of: (i) diacid residues consisting of at least 80 mole percent terephthalic acid residues, 2,6-naphthalene-dicarboxylic acid residues, 1,3-cyclohexanedicarboxylic acid residues, 1,4-cyclohexanedicarboxylic acid residues or a mixture thereof;   (ii) diol residues consisting of at least 50 mole percent of residues having the formula -O-(CH 2 ) p  -O-wherein p is 4 to 12; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR173## wherein B is a radical having the formula: ##STR174##  wherein R 16  is an unsubstituted or substituted alkyl, cycloalkyl or aryl radical; Ar is a divalent, aromatic, carbocyclic or heterocyclic radical; R 17  is a divalent linking group; and X is defined below;   R 1  is lower alkyl, lower alkoxy or halogen;   R 3  is a divalent organic group;   R 4 , R 5 , and R 6  are the same or different and each represents hydrogen or lower alkyl;   n is 0, 1, 2 or 3; and   X is hydroxy, carboxy or an ester radical having the formula: ##STR175## wherein R 22  is unsubstituted or substituted alkyl, cycloalkyl or aryl radical; provided that component (iii) constitutes at least 5.0 weight percent of the concentrate.   
     
     
       40. A colored semicrystalline powder according to claim 34 comprising a polyester having an inherent viscosity of at least 0.20 and a melting temperature of at least 110° C. comprised of: (i) diacid residues consisting of at least 80 mole percent terephthalic acid residues;   (ii) diol residues consisting of at least 80 mole percent of residues of 1,4.butanediol; and   (iii) residues of one or more methine colorant compounds having the formula: ##STR176## wherein R 1  is hydrogen, methyl, methoxy, ethoxy, or chloro;   R 3  -X is alkylene-OH, alkylene-O-alkylene-OH, ##STR177##  wherein each alkylene contains 2 to about 4 carbon atoms and each alkyl contains up to about 4 carbon atoms; and   R 5  and R 6  each is hydrogen or methyl; and   R 18  is lower alkyl; provided that component (iii) constitutes about 10 to 40 weight percent of concentrate.